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Application of a CC Bond‐Forming Conjugate Addition Reaction in Asymmetric Dearomatization of β‐Naphthols
Author(s) -
Yang Dongxu,
Wang Linqing,
Kai Ming,
Li Dan,
Yao Xiaojun,
Wang Rui
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201503056
Subject(s) - conjugate , enantioselective synthesis , chemistry , catalysis , magnesium , double bond , medicinal chemistry , organic chemistry , stereochemistry , mathematics , mathematical analysis
A CC bond‐forming conjugate reaction was successfully applied to the enantioselective dearomatization of β‐naphthols. A C(sp2)C(sp3) bond is formed by using propargylic ketones as reactive partners. Good to excellent Z / E ratios and ee values were obtained by employing an in situ generated magnesium catalyst. Further transformations of the Z ‐configured CC double bond in the products were achieved under mild reaction conditions. Moreover, the stereocontrolling element of this magnesium‐catalyzed dearomatization reaction was explored by computational chemistry.